CN109467737B - Method for preparing molecularly imprinted polymer by taking S-2-mercaptopropionic acid as chiral functional monomer - Google Patents
Method for preparing molecularly imprinted polymer by taking S-2-mercaptopropionic acid as chiral functional monomer Download PDFInfo
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Abstract
The invention relates to a method for preparing a molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer, belonging to the technical field of functional polymer materials. The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is used as a chiral functional monomer, S-naproxen is used as a template molecule, nano silica gel is used as a substrate, and a sacrificial silica gel framework method is adopted to prepare the molecularly imprinted polymer MIPs. The molecularly imprinted polymer prepared by the method has the characteristics of high imprinting rate and good selective adsorption performance, and can be used for chiral resolution of racemic naproxen.
Description
Technical Field
The invention relates to a method for preparing a molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer, belonging to the technical field of functional polymer materials.
Background
In recent years, the nonsteroidal drug Naproxen (alpha-methyl-6-methoxy-2-naphthylacetic acid, Naproxen) has the efficacy of relieving fever and easing pain, and is widely applied in the pharmaceutical industry. The alpha position of the naproxen derivative has a chiral carbon atom, a pair of optically active enantiomers exist, and research shows that R-configuration and S-configuration have different drug effects, and the drug effect of the S-configuration naproxen is 28 times that of the R-configuration. Naproxen is required to be marketed as a single enantiomer in order to reduce the toxic side effects of the isomers on the human body and the amount of the drug, and therefore, chiral resolution of a racemic mixture of naproxen is required.
Compared with other separation systems, molecularly imprinted polymers prepared by Molecular Imprinting Technology (MIT) show promising characteristics, such as low cost, easy synthesis, higher stability to complex chemical and physical environments, and better reusability. Thus, MIPs are widely used in many fields such as purification and separation, chiral recognition, chemical and biological sensing, and catalysis.
The preparation method of the Molecularly Imprinted Polymers (MIPs) comprises the following steps: precipitation polymerization, bulk polymerization, suspension polymerization, surface imprinting, and multi-step swelling polymerization. The sacrificial silica gel skeleton method in the surface imprinting method overcomes the defects that a bulk polymerization method and a precipitation polymerization method are difficult to remove template molecules, the polymer is irregular in shape, the experiment cost is high and the like, and becomes one of the most important methods for preparing the molecularly imprinted polymer. The document CN103193934A adopts a column chromatography silica gel surface molecular imprinting technology to prepare a molecularly imprinted polymer, but the obtained polymer has small specific surface area and low imprinting rate, so that the specific adsorption capacity of the polymer is influenced.
Disclosure of Invention
Aiming at the problems and the defects in the prior art, the invention provides a method for preparing a molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer. The invention takes nano silica gel as a carrier, S-2-mercaptopropionic acid as a chiral functional monomer, and adopts a sacrificial silica gel framework method to prepare the molecularly imprinted polymer, so that the invention has the characteristics of high imprinting rate and good selective adsorption performance, and can be used for chiral resolution of racemic naproxen. The invention is realized by the following technical scheme.
A method for preparing a molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is used as a chiral functional monomer, S-naproxen is used as a template molecule, nano silica gel is used as a substrate, and a sacrificial silica gel framework method is adopted to prepare the molecularly imprinted polymer MIPs.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving S-naproxen in a pore-foaming agent, adding a chiral functional monomer S-2-mercaptopropionic acid, oscillating for 2-3 h, adding a crosslinking agent ethylene glycol dimethacrylate and an initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an incubator tube filled with nano silica gel, carrying out ultrasonic treatment for 5-10 min, sealing, and carrying out water bath at 60-70 ℃ for 12-24 h to form a block polymer, namely molecularly imprinted polymer MIPs;
step 3, elution of the MIPs: and (3) placing the molecularly imprinted polymer MIPs obtained in the step (2) in a hydrofluoric acid solution to remove a silica gel framework, performing suction filtration, eluting the template molecules by using a mixed solution of methanol and acetic acid with the volume ratio of 9:1, then washing the template molecules to be neutral by using methanol, and performing vacuum drying for 24 hours to obtain the eluted molecularly imprinted polymer MIPs.
The pore-foaming agent in the step 1 is methanol, ethanol, acetonitrile, tetrahydrofuran, dichloromethane or N, N-dimethylformamide.
In the step 1, the molar ratio of S-naproxen, the chiral functional monomer S-2-mercaptopropionic acid and the cross-linking agent ethylene glycol dimethacrylate is 1: 2-8: 10-50.
In the step 1, the molar ratio of S-naproxen to the initiator azobisisobutyronitrile is 1: 0.06-0.12.
The above-mentioned S-naproxen is a commercially available reagent.
The invention has the beneficial effects that:
(1) the method adopts a sacrificial silica gel framework method and takes the nano silica gel as a matrix, and the prepared imprinted polymer has the advantages of large adsorption capacity, good imprinting effect, convenience in elution, high adsorption speed and the like, and solves the problems that the imprinted polymer prepared by the existing method has complicated post-treatment process, cannot be eluted due to too deep or too tight embedding of template ions, leakage in the use process and the like.
(2) The prepared molecularly imprinted polymer has good stability and repeatability, the resolution of racemic naproxen is successfully realized, the resolution factor reaches 2.31, the molecularly imprinted polymer has an obvious resolution effect, is expected to be used for chiral resolution of actual samples, and has a good application prospect.
Detailed Description
The present invention will be further described with reference to the following embodiments.
Example 1
The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as a substrate, and preparing the molecularly imprinted polymer MIPs by a sacrificial silica gel framework method.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (methanol), adding 2mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 3h, adding 10mmol of crosslinking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:4:20, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.12;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 5min, sealing, and carrying out water bath at 60 ℃ for 24h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.40g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules by using methanol until the template molecules are neutral, and performing vacuum drying for 24 hours to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 4.82. And the resolution factor of the molecularly imprinted polymer MIPs reaches 2.31, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
Example 2
The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as a substrate, and preparing the molecularly imprinted polymer MIPs by a sacrificial silica gel framework method.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (ethanol), adding 1mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 2 hours, adding 10mmol of cross-linking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:2:20, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.06;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 10min, sealing, and carrying out water bath at 70 ℃ for 24h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.33g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules by using methanol until the template molecules are neutral, and performing vacuum drying for 24 hours to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 1.18. And the resolution factor of the molecularly imprinted polymer MIPs reaches 1.56, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
Example 3
The molecular imprinting polymerization is prepared by taking S-2-mercaptopropionic acid as a chiral functional monomerA method of making a composition comprising the steps of: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as a substrate, and preparing the molecularly imprinted polymer MIPs by a sacrificial silica gel framework method.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (tetrahydrofuran), adding 4mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 3 hours, adding 5mmol of crosslinking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:8:10, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.09;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 5min, sealing, and carrying out water bath at 70 ℃ for 24h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.31g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules by using methanol until the template molecules are neutral, and performing vacuum drying for 24 hours to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 1.12. And the resolution factor of the molecularly imprinted polymer MIPs reaches 1.37, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
Example 4
The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as matrix, and adopting sacrificial silica gel skeleton method to prepare the molecularly imprinted polymerThe substance MIPs.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (tetrahydrofuran), adding 2mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 3 hours, adding 5mmol of crosslinking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking uniformly to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:4:10, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.09;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 5min, sealing, and carrying out water bath at 60 ℃ for 12h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.40g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules by using methanol until the template molecules are neutral, and performing vacuum drying for 24 hours to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 2.15. And the resolution factor of the molecularly imprinted polymer MIPs reaches 2.06, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
Example 5
The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as a substrate, and preparing the molecularly imprinted polymer MIPs by a sacrificial silica gel framework method.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (dichloromethane), adding 2mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 3 hours, adding 20mmol of crosslinking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:4:40, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.09;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 10min, sealing, and carrying out water bath at 70 ℃ for 24h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.38g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules to be neutral by using methanol, and performing vacuum drying for 24h to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 1.22. And the resolution factor of the molecularly imprinted polymer MIPs reaches 1.69, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
Example 6
The method for preparing the molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer comprises the following steps: s-2-mercaptopropionic acid is taken as a chiral functional monomer, S-naproxen (S-Npx) is taken as a template molecule, and Nano silica gel (Nano-SiO)215 nm) as a substrate, and preparing the molecularly imprinted polymer MIPs by a sacrificial silica gel framework method.
The method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving 0.5mmol of S-naproxen in 20mL of pore-foaming agent (N, N-dimethylformamide), adding 2mmol of chiral functional monomer S-2-mercaptopropionic acid, oscillating for 2.5h, adding 25mmol of crosslinking agent ethylene glycol dimethacrylate and initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution; wherein the molar ratio of the S-naproxen to the chiral functional monomer S-2-mercaptopropionic acid to the crosslinking agent ethylene glycol dimethacrylate is 1:4:50, and the molar ratio of the S-naproxen to the initiator azobisisobutyronitrile is 1: 0.09;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an amplex tube filled with nano silica gel (10 g of nano silica gel is filled in a 40mL amplex tube), carrying out ultrasonic treatment for 7min, sealing, and carrying out water bath at 65 ℃ for 18h to form a block polymer, namely Molecularly Imprinted Polymer (MIPs);
step 3, elution of the MIPs: and (3) placing 0.40g of the MIPs obtained in the step (2) in 100mL of hydrofluoric acid solution (the concentration of the hydrofluoric acid solution is 448 g/L) to remove a silica gel framework, performing suction filtration, eluting the template molecules by using 150mL of mixed solution of methanol and acetic acid with the volume ratio of 9:1, washing the template molecules by using methanol until the template molecules are neutral, and performing vacuum drying for 24 hours to obtain the eluted MIPs.
The molecularly imprinted polymer MIPs prepared in the embodiment can adsorb S-naproxen, and the imprinting factor can reach 1.28. And the resolution factor of the molecularly imprinted polymer MIPs reaches 1.78, and the molecularly imprinted polymer MIPs has an obvious resolution effect.
In the above examples, the reagents are analytically pure reagents except for the reagents of the specified labeled concentrations.
While the present invention has been described in detail with reference to the specific embodiments thereof, the present invention is not limited to the embodiments described above, and various changes can be made without departing from the spirit of the present invention within the knowledge of those skilled in the art.
Claims (4)
1. A method for preparing a molecularly imprinted polymer by taking S-2-mercaptopropionic acid as a chiral functional monomer is characterized by comprising the following steps: s-2-mercaptopropionic acid is used as a chiral functional monomer, S-naproxen is used as a template molecule, nano silica gel is used as a substrate, and a sacrificial silica gel framework method is adopted to prepare Molecularly Imprinted Polymers (MIPs);
the method comprises the following specific steps:
step 1, preparation of a pre-polymerization solution: completely dissolving S-naproxen in a pore-foaming agent, adding a chiral functional monomer S-2-mercaptopropionic acid, oscillating for 2-3 h, adding a crosslinking agent ethylene glycol dimethacrylate and an initiator azobisisobutyronitrile, and shaking up to form a pre-polymerization solution;
step 2, preparation of MIPs: transferring the prepolymerization solution obtained in the step 1 into an incubator tube filled with nano silica gel, carrying out ultrasonic treatment for 5-10 min, sealing, and carrying out water bath at 60-70 ℃ for 12-24 h to form a block polymer, namely molecularly imprinted polymer MIPs;
step 3, elution of the MIPs: and (3) placing the molecularly imprinted polymer MIPs obtained in the step (2) in a hydrofluoric acid solution to remove a silica gel framework, performing suction filtration, eluting the template molecules by using a mixed solution of methanol and acetic acid with the volume ratio of 9:1, then washing the template molecules to be neutral by using methanol, and performing vacuum drying for 24 hours to obtain the eluted molecularly imprinted polymer MIPs.
2. The method for preparing the molecularly imprinted polymer by using S-2-mercaptopropionic acid as a chiral functional monomer according to claim 1, wherein the method comprises the following steps: the pore-foaming agent in the step 1 is methanol, ethanol, acetonitrile, tetrahydrofuran, dichloromethane or N, N-dimethylformamide.
3. The method for preparing the molecularly imprinted polymer by using S-2-mercaptopropionic acid as a chiral functional monomer according to claim 1, wherein the method comprises the following steps: in the step 1, the molar ratio of S-naproxen, the chiral functional monomer S-2-mercaptopropionic acid and the cross-linking agent ethylene glycol dimethacrylate is 1: 2-8: 10-50.
4. The method for preparing the molecularly imprinted polymer by using S-2-mercaptopropionic acid as a chiral functional monomer according to claim 1, wherein the method comprises the following steps: in the step 1, the molar ratio of S-naproxen to the initiator azobisisobutyronitrile is 1: 0.06-0.12.
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